The periodic table still provides guidance
to modern research (1-7) 130 years after its
original development. It is of lasting and continuing value because it can include
large amounts of information about each of the elements, with similar elements
grouped, and the groups are juxtaposed in order to facilitate pattern recognition and
differentiation. This in turn facilitates
visualization, retention, understanding, and use of the
data presented. One very important function of the periodic table in research has been as
a data organizer and systematizer. It is not merely a teaching device (such as
flash cards), a data holder (such as a lookup
table), or a calculation aid (such as a slide rule),
although the periodic table certainly can function in each of these roles. It is
well-known that Mendeleev used his periodic table
to predict the existence of undiscovered elements. In doing so, he charted known
information in a highly systematic way, which provided a map leading to exploration
of new territory.

Although the events have become
legendary, application of this technique to other areas of chemistry is not one routinely reported. However, it should be of great
utility in dealing with projects having a broad range. These projects could be sets
with many members, such as investigations encompassing many different elements,
reactions, mechanisms, etc.

Organic chemistry is often described
as a difficult discipline because there is such a large amount of data to be learned.
Particular attention is paid to learning
mechanisms of the reactions, which often involve
nucleophiles and electrophiles. In order to
facilitate pattern recognition and retention of nucleophiles, electrophiles, and the
mechanisms describing their reactions, we developed a Nucleophile/Electrophile
(Nu/E) Reaction Guide (8-12) containing a page
of nucleophiles and a page of electrophiles, grouped according to similarities. The
two pages can be juxtaposed in order to visualize the mechanisms of reactions of
nucleophiles and electrophiles common to organic chemistry and to facilitate remembering
and differentiating (a) the electrophiles and nucleophiles, (b) the active site(s) in each,
and (c) the arrow(s) designating the flow of electrons in the reaction of the two. An addi-

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tional result of aligning nucleophiles
and electrophiles in order to visualize reactions, was identification of potential reactions
not covered in the classroom. Thus, just as in the original development of the
periodic table, with the "holes" predicting
undiscovered elements, users of this guide quickly identified potential reactions that had
not been revealed to them. Thus, the enterprise led to a discovery that the organization
and systematization techniques applied to previous territories can also be applied
more universally, to aspects of organic chemistry.

However, reactions of electrophilic
aromatic substitution (EAS) are somewhat more complicated. In order to make the data
manageable, most treatments apply some organization, such as categorizing the
reactions with respect to the patterns exhibited in
the mechanisms, and by the effects of the substituents in the aromatic compounds on
the reaction rate and regiochemistry. However, usually a separate reaction which
provides the active reagent must also be
considered, as well as the active site(s) in the
reactant, the active site(s) in the reagent, and
stabilizing charge delocalization caused by induction, conjugation, or both, in the
intermediate. The multitude of variables in these
reactions made it impossible to include EAS reactions as an entry in the Nu/E
Reaction Guide. Therefore, it was necessary to develop a separate but similar
organizational device for EAS.

This manuscript presents an evaluation of one hand-held device, the Nu/E
Reaction Guide for facilitating students'
understanding of reaction mechanisms in organic
chemistry. (9,10) Future similar investigations
are planned for the EAS Tool.

The participants were enrolled in a
first-semester organic chemistry course for science and engineering majors at a
comprehensive public university. The sample consisted of 126 students; 63 were assigned to a control group, 17 were assigned to out-of-class device group, 25 were assigned to
in-class device group, and 21 were assigned
to use the device both in class and out of class (Table 1). Assignments were random,
and the course met for a total of 150 min/wk for the 15-wk semester. There were four
different groups organized according to device use. Group YY saw demonstrations of
how to use the device in class, mimicked the use of the device in class, and then used it
unsupervised outside class. Each student in an in-class device group (Group YN) saw
the demonstration, mimicked the demonstration with a device, continued to use the
device in class, but did not use the device outside class. Each student in the
out-of-class device group (Group NY) saw demonstrations of how to use the device in class
and then used the device unsupervised outside class. The students in the control
group (Group NN) did not use the guide at all. Thus, the uses of the device by Group
YY would be a combination of those of the in class group (Group YN) and of the out
of class group (Group NY) described above.

The experimental design is a
posttest-only control group design for both
content knowledge and problem solving. The questions used in the posttest are given in
Table 2. A Control Unit Achievement Test (CUAT)
(13) showed that the groups were approximately equivalent in their chemical
knowledge before the treatment. There were no other variables in the groups, such as
different TA's. Periodic checks were made to insure no use of the device by the Group
NN students through sharing with students from other groups.

The results from the Nu/E
Reaction Guide study are shown in Table 1, and the test questions are in Table 2. The
questions were designed to determine student knowledge of various aspects of
nucleophiles, electrophiles, and reactions and/or
mechanisms involving nucleophiles and electrophiles. The percent correct
response for each test question for each of the
sample groups, Group YY, YN, NY, and NN (columns 1-3 and 5), as well as for a
weighted average of all groups using the device in
any manner (column 4), is shown (Table 1).

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The CUAT scores for the groups, the
last row of entries in Table 1, indicate that
there was no difference between the three treatment groups and the control group:
YY, 66.1%; YN, 69.2%; NY, 62.8%; NN, 66.8%. The weighted average for all groups
using the device is 66.4%, almost identical to
that of the control group.

The average of the five questions for
each group is given in Table 1 (Ave Q1-Q5). The results are as follows: Group YY,
70.5%; Group YN, 73.6%, Group NY, 73.0%, Group NN, 64.1%. All three of the groups
which used the Nu/E Guide (Groups YY, YN, and NY) performed significantly better
than those of the control group (Group NN), and the weighted average of all groups using
the device is 72.4%. Curiously, of the three groups using the device, the group
which used the device both in and out of class scored marginally lower than the other two.
The control group had the lowest average score on every test question except one
(Q3), and in that one it had the next to the
lowest score. Comments of some students using the Nu/E Guide in List 1 indicate that the students valued the device.

If the average results (Ave Q1-Q5)
are normalized by using factors obtained from the CUAT scores (control score -
group score), the corrected averages (corrected average Q1-Q5) become Group YY,
71.2%; Group YN, 71.2%; Group NY, 77.0%; Group NN, 64.1%. This analysis of the
results shows that Group NY shows the most improvement from use of the Nu/E Guide.
The reason for this may be that the student using the guide only out of class, puts
more thought into determining how to use the guide, and did not merely follow the
demonstration. Therefore, these students learned more from the independent effort invested.

II. ELECTROPHILIC AROMATIC
SUBSTITUTION (EAS) TOOL

A prototype for such a device was
created and used in the classroom and described at a national ACS meeting.
(10) It was compared (11, 12) to a slide rule,
because it consists of two surfaces which slide
against each other with arrows to align in order to

pair reactants. The device is similar to a
slide rule, but different as it also contains a
great deal of organized and systematized information. As a result of the comparison,
(11, 12) we received inquiries about the device
from universities, from business, but mostly from industry. Because of the apparent
interest in the device, we present a description of
it and of the application of the organization and systematization techniques to EAS.

The device consists of two sheets of
card stock, presenting EAS data in an organized fashion to facilitate pattern recognition
and retention. One sheet can be placed over the other in order to visualize the
mechanism between the substituted aromatic
compound selected and the chosen reagent. On separate pages, it gives two aspects of EAS
and then demonstrates interactively how these aspects inter-relate. The two aspects are:
(a) the substitution itself, including the
identity of the electrophile, the reagent(s) needed
to generate it, and the substituent in the product and (b) the electronic effects of the
groups in the aromatic compounds on the intermediate(s) and the structure of the
product.

Sheet A (Figure 1) presents a
discussion of and a table of representative
electrophiles, the reagents needed to generate them,
and the general class of product obtained from the reaction of each electrophile with an
aromatic compound. In the first column, the electrophile (E or E+) undergoing attack
by the p-electrons of the aromatic compound is listed. Each electrophile in the "E or
E+" column has a head half of an arrow
leading from the side of the page and pointing to
an atom which is the reactive site in the electrophile, usually the atom bearing
the highest amount of positive charge. This atom is the one to which the aromatic
ring will become attached. In the second column are the reagents which generate
the electrophiles in the first column. The third column lists the final product obtained
by treating the aromatic compound with the reagent(s) in the second column. On
the obverse of Sheet A are an introduction and additional discussion, including
definitions of the aromatic ring positions relative to
the group in the reactant, and an explanation of the four different types of electronic
effects caused by substituents in the aromatic
reactants. These four different categories of
electronic effects are (a) ERG (-system) = Electron Releasing Group via the
-system, (b) ERG (-system) = Electron Releasing
Group via the -system, (c) ECG = Electron Conjugating Group, and (d) EWG = Electron
Withdrawing Group.

Sheet B bears a table consisting of
columns of information concerning EAS in general. Information is categorized with
respect to the type of electronic effects caused by
the substituents in the aromatic reactant; the members and characteristics of each
category are placed next to each other to facilitate pattern recognition and thereby
retention of the data presented. The first column contains a series of mono-substituted
aromatic compounds as reactants categorized according to the type of electronic
effects (defined at the bottom of the table)
caused by the substituent present. Examples of
substituents causing each type of electronic effect and a general description of its
characteristics are below each substituted
aromatic compound. The arrow leading from the reactant molecule to E+ represents the
electrophilic attack of the p electrons upon the
general electrophile (the rate-determining step of the reaction). The second column has
the most stable resonance structure(s) of the most-favored intermediate(s) of the
reaction, with arrows depicting electron
withdrawal or donation justifying why that
intermediate is disfavored. Since the position of
the C-E bond has been established by this point, each intermediate leads logically to the
major product(s), which are given in the third column. The fourth column shows the
disfavored intermediate, with arrows depicting electron withdrawal or donation and
justifying why that intermediate is disfavored.

In order to consider the reaction of a
specific electrophile with a type of aromatic reactant under the effects of its
substituent(s), it is necessary to juxtapose Sheet A and
Sheet B. Bringing together the two reactants enables one to visualize the mechanism of
the rate-determining step of a specific reaction while considering and tracking all of
the variables involved. Attack at each specific

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E or E+ is shown in the far left column
of Sheet A, with arrows leading to each from the edge of the card. Attack by the
aromatic compound upon a general electrophile E+ is shown in the left one-third of Sheet B,
with arrows leading from the aromatic compound to E+. Therefore, in order to visualize
the rate-determining step of a specific reaction, place Sheet A over the right two-thirds
of Sheet B and align the head of the appropriate arrow on Sheet A with the base of
the appropriate arrow on Sheet B. The steps involved in this process are (a) select the
aromatic structure bearing the desired group type, (b) locate the corresponding base
half of the arrow desired, (c) select the desired reagent(s) to be used or the electrophile
provided, (d) determine the corresponding head half of the arrow desired, and (e)
visualize the mechanism leading to the correct intermediate(s) by placing Sheet A over
the right two-thirds of Sheet B and aligning the selected head half-arrow with the
selected base half-arrow.

Two examples demonstrating the use
of the EAS organization device to visualize the mechanistic attack of the aromatic
compound upon the electrophile ( E or E+), leading to the intermediate and product with
the proper regiochemistry are given on the reverse of Sheet B in the device. They are
(a) Friedel-Crafts acylation of a halobenzene and (b) chlorination of phenol. The
latter example is reproduced in Figure 1.

The effect upon learning brought
about by using a teaching device has been measured. This device, the Nu/E Guide,
consists of two sheets of card stock, one with nucleophiles, and one with electrophiles.
The student can visualize a reaction mechanism by juxtaposing the two sheets in
order to line up the selected nucleophile and the selected electrophile. Analysis of the
results of the study shows that students using the device outside of class scored higher on
pertinent exam questions (77%) than students not using the device (64%). The reason
for this may be that students using the guide only out of class, put more thought into de-

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termining how to use the guide, and did
not merely follow the demonstration. Therefore, these students learned more from the
independent effort invested.

The success of the Nu/E
Guide prompted development of a similar device dealing with electrophilic aromatic
substitution (EAS), called the EAS Tool. To use this new device, one sheet is placed over
the other in order to visualize the mechanism between the substituted aromatic
compound selected and the chosen reagent. Testing
of the EAS Tool is in progress.

List 1. Comments of organic chemistry
students using the Nucleophile/Electrophile Reaction Guide.

"I think the Nucleophile/Electrophile
Reaction Guide is very beneficial in getting an overall view of the course's reactions. It
provides us with an easy method to figure out the reactions in the course."

"One of my big problems was
visualization of reactions. The
Nucleophile/Electrophile Reaction Guide helped me to see where
reactive sites were on the different functional groups."

"The Nucleophile/Electrophile
Reaction Guide has helped immensely with my ability to learn and understand organic
reactions. Although it does not give the detailed mechanisms, the table is a great tool to
learn the fundamental reactions of Organic Chemistry. The ability to visualize which
nucleophiles will react with the electrophiles has helped me build a foundation for my
study of organic chemistry."

"The Nucleophile/Electrophile
Reaction Guide helped me see how all of the
reactions were interrelated and how there was a
pattern between the reactions."

"I like the fact that the guide provides a
condensed reference to facilitate learning the reactions. The sheets condense
multiple chapters of information, and thus make it

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easier to find a specific reaction."

"The Nucleophile/Electrophile
Reaction Guide was very helpful in the respect of
time saving capabilities. For instance, all electrophile/nucleophile reactions
which can occur are readily available for examination on two sheets of paper. One
doesn't have to locate all reactions throughout
the text for this valuable information."

"The Nucleophile/Electrophile
Reaction Guide allows students to see the various
reaction pathways that are possible."

"Organic chemistry has so much
memorization. This Guide has provided a system to weeks of class material."

"The use of the
Nucleophile/Electrophile Reaction Guide has made recognition
of such reactions quicker and simpler to understand."

"The Nucleophile/Electrophile
Reaction Guide has saved a great deal of time in studying these types of reactions."

"Nucleophile/Electrophile Reaction
Guide is a most valuable tool for chemistry students. It has been of great benefit to me,
and I'm sure it will be of great benefit to future students."

"The methods of study needed for
Organic Chemistry are often as difficult as the
subject itself. To quote a recent marketing campaign, often "the system is the solution."
Much of chemistry study is often finding patterns or systems for understanding.
The Nucleophile/Electrophile Reaction Guide provides a system in a format that easily,
as well as expeditiously, provides one with a system for effective learning."